JPH11140064A - Production of 1,2,3-thiadiazole derivative and its intermediate - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain the subject compound that is useful for herbicide and microbicide by allowing a specific compound to react with a hydrazine in an inert solvent to prepare an intermediate followed by reaction of the intermediate with thionyl chloride or sulfur dioxide. SOLUTION: The reaction between a compound of formula I (R1 is H, a 1-6C alkyl, a 3-7C cycloalkyl; R2 is H, a 1-20C alkyl, a 2-20 alkenyl; Y is -O, -S- or the like) and a hydrazine of formula II (R3 is a 1-20C alkylcarbonyl, a 3-12C cycloalkylcarbonyl) is carried out to prepare a compound of formula III. The compound of formula III is isolated, or not isolated, and allowed to react with thionyl chloride or sulfur dichloride to prepare 1,2,3-thiadiazole derivative. The compound of formula III is unknown, thus the objective compound is obtained that is useful as a herbicide, a plant growth regulator and a microbicidal agent.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

TECHNICAL FIELD The present invention relates to a novel method for producing 1,2,3-thiadiazole derivatives, intermediate compounds thereof, and methods for producing them.

[0002]

2. Description of the Related Art JP-A-54-9272 and JP-A-55-9272.
JP-A-124773 and JP-A-8-325110 disclose methods for producing 1,2,3-thiadiazole derivatives.

[0003]

DISCLOSURE OF THE INVENTION The present inventors diligently seek to find a novel method for producing 1,2,3-thiadiazole derivatives useful as herbicides, plant growth regulators and fungicides disclosed in the prior art. As a result of repeated studies, they have found that the production method of the present invention is a novel production method not described in the literature, and that the intermediate compound is also a novel compound except for some compounds, and completed the present invention. It is a thing.

[0004]

According to the present invention, as a first production method, a compound represented by the general formula (IV):

Embedded image(Where R₁Is a hydrogen atom, C₁-C₆ Alkyl group or C_Three-C₇
R represents a cycloalkyl group;_TwoIs a hydrogen atom, C₁-C₂₀Al
Kill group, halo C₁-C₂₀Alkyl group, C_Two-C₂₀Alkenyl group,
Halo C_Two-C₂₀Alkenyl group, C_Two-C₂₀Alkynyl group, halo C_Two
-C₂₀Alkynyl group, C_Three-C₁₂Cycloalkyl group, C₁-C₆A
Lucoxy C₁-C₆Alkyl group, C₁-C₆Alkoxy C₁-C₆A
Lucoxy C₁-C₆Alkyl group, carboxy C₁-C₆Alkyl
Group, C₁-C ₂₀Alkoxycarbonyl C₁-C₆Alkyl group,
Lubamoyl C₁-C₆Alkyl group, same or different
C₁-C₁₂Alkyl group, phenyl group, or halogen atom
Or C₁-C₆Phenyl group substituted by alkyl group
Substituted carbamo having one or two substituents selected from
Il C₁-C₆Alkyl group, cyano C₁-C₆Alkyl group, C₁-C
₆Alkylcarbonyloxy C₁-C₆Alkyl group, phenyl
Lecarbonyloxy C₁-C₆Alkyl group, same or different
Halogen atom, cyano group, nitro group, C₁-C₆
Alkyl group, halo C₁-C₆Alkyl group, C₁-C₆Alkoxy
Group, halo C₁-C₆Alkoxy group or C₁-C₁₂Alkoxycal
Having 1 to 5 substituents selected from a bonyl group on the ring
Substituted phenylcarbonyloxy C₁-C₆Alkyl group,
Phenyl group, which may be the same or different, a halogen atom,
Ano group, nitro group, C₁-C₆Alkyl group, halo C₁-C₆Al
Kill group, C₁-C₆Alkoxy group, halo C₁-C₆Alkoxy group
Or C₁-C₁₂1 to 1 selected from an alkoxycarbonyl group
Substituted phenyl group having 5 substituents, phenyl C₁-C₆
An alkyl group, which may be the same or different, a halogen atom,
Cyano group, nitro group, C₁-C₆Alkyl group, halo C₁-C₆A
Lucyl group, C₁-C₆Alkoxy group, halo C₁-C₆Alkoxy
Group or C₁-C₁₂1 selected from an alkoxycarbonyl group
Substituted phenyl C having up to 5 substituents on the ring₁-C₆Al
Kill group,

[0005] C₁-C₆Alkylcarbonylamino C₁-C₆A
Alkyl group, phenylcarbonylamino C₁-C₆Alkyl
Groups, which may be the same or different, a halogen atom, a cyano
Group, nitro group, C₁-C₆Alkyl group, halo C₁-C₆Alkyl
Group, C₁-C₆Alkoxy group, halo C₁-C ₆An alkoxy group or
C₁-C₁₂1 to 5 selected from alkoxycarbonyl groups
Substituted phenylcarbonylamino having a substituent on the ring
C₁-C₆An alkyl group, which may be the same or different,
One or more hetero atoms selected from the group consisting of
5 to 6-membered heterocyclic ring having a hydrogen atom, which may be the same or different
, Halogen atom, cyano group, nitro group, C₁-C₆Archi
Le group, halo C₁-C₆Alkyl group, C₁-C₆Alkoxy group, ha
B c₁-C₆Alkoxy group or C₁-C₁₂Alkoxycarbonyl
Having 1 to 5 substituents selected from the group
Same or different selected from atoms, sulfur atoms or nitrogen atoms
Optionally substituted 5-6 membered with one or more heteroatoms
Heterocyclic, may be the same or different, oxygen atom, sulfur atom
Or has one or more hetero atoms selected from nitrogen atoms
5-6 membered heterocyclic C₁-C₆Alkyl groups, identical or different
Good, halogen atom, cyano group, nitro group, C₁-C₆A
Lucyl group, halo C₁-C₆Alkyl group, C₁-C₆Alkoxy
Group, halo C₁-C₆Alkoxy group or C₁-C₁₂Alkoxycal
Having 1 to 5 substituents selected from a bonyl group on the ring;
Selected from an oxygen atom, a sulfur atom and a nitrogen atom
Substitution with one or more heteroatoms which may be one or different
5-6 membered heterocyclic C₁-C₆Alkyl group, same or different
Well selected from oxygen, sulfur or nitrogen
5- to 6-membered heterocycle C having one or more heteroatoms₁-C₆Cal
A bonyloxyalkyl group, which may be the same or different,
Logen atom, cyano group, nitro group, C₁-C₆Alkyl group,
Halo C₁-C₆Alkyl group, C₁-C₆Alkoxy group, halo C₁-C
₆Alkoxy group or C₁-C₁₂From an alkoxycarbonyl group
Having 1 to 5 substituents selected on the ring, an oxygen atom,
Same or different selected from sulfur atom or nitrogen atom
Substituted 5- to 6-membered heterocycles having one or more heteroatoms
Carbonyloxy C₁-C₆Alkyl groups, identical or different
Also selected from oxygen, sulfur or nitrogen atoms
5- or 6-membered heterocyclic carbonyl having one or more heteroatoms
Lumino C₁-C₆An alkyl group or

The halogen atom, cyano group, nitro group, C ₁ -C ₆ alkyl group, halo C ₁ -C
₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group or C ₁ -C ₁₂ alkoxycarbonyl group having 1 to 5 substituents on the ring, an oxygen atom, The same or different 1 selected from a sulfur atom or a nitrogen atom
Represents a substituted 5- to 6-membered heterocyclic carbonylamino C ₁ -C ₆ alkyl group having the above heteroatom, and Y represents —O— or —S—
Or —N (R ₄ ) — (wherein R ₄ is a hydrogen atom or C ₁ -C ₆
Shows an alkyl group. ). ) And a compound of the general formula (III)

[0007]

[Image Omitted] R_ThreeNHNH_Two (III) (wherein, R_ThreeIs C₁-C₂₀Alkylcarbonyl group, halo C₁-C
₂₀Alkylcarbonyl group, C_Three-C₁₂Cycloalkylcarbo
Nyl group, hydroxy C₁-C₂₀Alkylcarbonyl group, shea
No C₁-C₂₀Alkylcarbonyl group, C₁-C₂₀Alkoxycal
Bonyl group, C₁-C ₂₀Alkoxy C₁-C₂₀Alkylcarbonyl
Group, a phenylcarbonyl group, which may be the same or different,
Halogen atom, cyano group, nitro group, C₁-C₆Alkyl
Group, halo C₁-C₆Alkyl group, C₁-C₆Alkoxy group, halo
C₁-C₆Alkoxy group or C₁-C₁₂Alkoxycarbonyl group
Substituted 1 to 5 substituents on the ring selected from
Phenylcarbonyl group, phenyl C₁-C₆Alkyl carboni
Groups, which may be the same or different, a halogen atom, a cyano
Group, nitro group, C₁-C₆Alkyl group, halo C₁-C₆Alkyl
Group, C₁-C₆Alkoxy group, halo C₁-C₆An alkoxy group or
C₁-C₁₂1 to 5 selected from alkoxycarbonyl groups
Phenyl C having a substituent on the ring₁-C₆Alkylka
Rubonyl group, carbamoyl group, C₁-C₂₀Alkylsulfoni
Le group, halo C₁-C ₂₀Alkylsulfonyl group, C_Three-C₁₂Cyclo
Alkylsulfonyl group, phenylsulfonyl group or the same
Or a halogen atom, a cyano group,
Toro group, C₁-C₆Alkyl group, halo C₁-C₆Alkyl group, C₁
-C₆Alkoxy group, halo C₁-C₆Alkoxy group or C₁-C₁₂
1 to 5 substitutions selected from alkoxycarbonyl groups
A substituted phenylsulfonyl group having a group on the ring is shown. )
Reacting with a hydrazine represented by the general formula (II)

[0008]

Embedded image (Wherein R ₁ , R ₂ , R ₃ and Y are as defined above), and the compound (II) is reacted with thionyl chloride or sulfur dichloride without isolation. General formula (I)

Embedded image (Wherein R ₁ , R ₂ and Y are the same as described above), and a general formula (II) which is an intermediate of the method for producing a 1,2,3-thiadiazole derivative

[0009]

Embedded image (Wherein R ₁ , R ₂ , R ₃ and Y are the same as described above) and a method for producing the same, as a second production method, a compound represented by the general formula (I ′)

Embedded image (Wherein, R ₁ is as defined above, and R ₂ ′ represents a C ₁ -C ₃ alkyl group) and a 1,2,3-thiadiazole derivative represented by the general formula (III ′):

[0010]

Embedded image wherein an amine represented by R ₄ —NH—R ₂ (III) (wherein R ₂ and R ₄ are as defined above) is reacted in the presence of a base or an acid. General formula (I '')

Embedded image (Wherein R ₁ , R ₂ and R ₄ are the same as described above).

A typical manufacturing method of the present invention can be exemplified as follows when illustrated, for example. Manufacturing method 1.

Embedded image (In the formula, R ₁ , R ₂ , Y and R ₃ are the same as described above.)

The compound represented by the general formula (IV) and the compound represented by the general formula (II)
Reacting with a hydrazine represented by the formula (I) in the presence of an inert solvent to obtain a compound represented by the general formula (II),
By isolating (II) or not isolating it and reacting it with thionyl chloride or sulfur dichloride, a 1,2,3-thiadiazole derivative represented by the general formula (I) can be produced. (1) General formula (IV) → General formula (II) The inert solvent used in the present reaction may be any solvent which does not significantly inhibit the progress of the present reaction, for example, alcohols such as methanol, ethanol and propanol. , Aromatic hydrocarbons such as benzene, toluene and xylene, halogenated hydrocarbons such as chloroform, dichloroethane and chlorobenzene, and linear or cyclic ethers such as tetrahydrofuran, diethyl ether and dioxane; amides such as dimethylformamide and dimethylacetamide And esters such as ethyl acetate, and inert solvents such as dimethylsulfoxide and water. These inert solvents can be used alone or in combination of two or more. Preferred inert solvents include water or alcohols.

Since this reaction is an equimolar reaction, the general formula (I
The compound represented by V) and the hydrazine represented by the general formula (III) may be used in equimolar amounts, but any one of the reactants may be used in excess. In order to promote the progress of this reaction, a catalyst such as sulfuric acid or toluenesulfonic acid may be added, and the amount of the catalyst used may be a catalytic amount. The reaction temperature of this reaction can be appropriately selected from the range of −20 ° C. to 100 ° C., and is preferably in the range of 20 ° C. to 60 ° C. The reaction time is not fixed depending on the reaction temperature, the reaction scale and the like, but may be in the range of several minutes to 48 hours. After completion of the reaction, the target product can be produced by isolating the target product from the reaction system containing the target product by a conventional method and, if necessary, purifying the product by a method such as recrystallization or column chromatography. Further, the compound can be subjected to the next step without isolation from the reaction system containing the target compound. The compound represented by the general formula (IV), which is a starting compound for this reaction, is described in Org. Synth. Col
l. Vol. III, 10 and J, Chem. Soc. ,
1908 , 946.

(2) General formula (II) → General formula (I) The inert solvent used in this reaction may be any solvent which does not react with the reactant thionyl chloride or sulfur dichloride. , Toluene, xylene and other aromatic hydrocarbons, chloroform, dichloroethane, chlorobenzene and other halogenated hydrocarbons, tetrahydrofuran,
Inert solvents such as linear or cyclic ethers such as diethyl ether and dioxane can be exemplified, and these inert solvents can be used alone or in combination of two or more. Preferred inert solvents include aromatic hydrocarbons. Further, by using an excess of thionyl chloride or sulfur dichloride as a reactant as an inert solvent in this reaction, both the reactant and the inert solvent can be made to function. The amount of thionyl chloride or sulfur dichloride used as a reactant in this reaction is at least equimolar to the compound represented by the general formula (II), and is preferably 2 to 2 or more.
What is necessary is just to use in the range of 3 equivalents. The reaction temperature of this reaction is-
It can be carried out by appropriately selecting from the range of 20 ° C. to 100 ° C., and preferably in the range of 20 ° C. to 60 ° C.
The reaction time is not fixed depending on the reaction temperature, the reaction scale and the like, but may be in the range of several minutes to 48 hours. After completion of the reaction, the target product can be produced by isolating the target product from the reaction system containing the target product by a conventional method and, if necessary, purifying the product by a method such as recrystallization or column chromatography.

Manufacturing method 2.

Embedded image (In the formula, R ₁ , R ₂ , R ₂ ′ and R ₄ are the same as described above.) A 1,2,3-thiadiazole derivative represented by the general formula (I ′) and an amine represented by the general formula (V) Are reacted in the presence of a base or an acid to give a compound represented by the general formula (I '')
A 2,3-thiadiazole derivative can be produced. The inert solvent used in this reaction may be any solvent that does not significantly inhibit the progress of this reaction, and examples thereof include aromatic hydrocarbons such as benzene, toluene, and xylene, and halogenated hydrocarbons such as chloroform, dichloroethane, and chlorobenzene. And linear or cyclic ethers such as tetrahydrofuran, diethyl ether, and dioxane; amides such as dimethylformamide and dimethylacetamide; esters such as ethyl acetate; and inert solvents such as dimethylsulfoxide. The inert solvents can be used alone or in combination of two or more. Preferably, for example, when the reaction is performed under acidic conditions, aromatic hydrocarbons or halogenated hydrocarbons are used.When the reaction is performed under basic conditions, ethers, dimethylformamide or dimethyl sulfoxide is preferably used. .

Examples of the acid or base used in this reaction include Bronsted acids such as sulfuric acid and acetic acid, and Lewis acids such as aluminum chloride and titanium tetrachloride, preferably aluminum chloride. Examples of the base include alcoholates such as sodium methoxide and potassium tert-butoxide, and hydrides of alkali metals such as sodium hydride, and preferably sodium hydride. Furthermore, an organic base such as ammonia, ethylenediamine, triethylamine, or dimethylaniline can be added to these bases and reacted. The amount of the acid or the base used is 0.01 to 1,2,3-thiadiazole derivative represented by the general formula (I ').
What is necessary is just to select and use suitably from the range of 10 to 10 equivalents. Since this reaction is an equimolar reaction, 1,1 represented by the general formula (I ′)
The 2,3-thiadiazole derivative and the amine represented by the general formula (V) may be used in equimolar amounts, but any of the reactants may be used in excess. The reaction temperature of this reaction can be appropriately selected from the range of −20 ° C. to 100 ° C., and is preferably in the range of 20 ° C. to 100 ° C. The reaction time is not fixed depending on the reaction temperature, the reaction scale and the like, but may be in the range of several minutes to 48 hours. After completion of the reaction, the target product can be produced by isolating the target product from the reaction system containing the target product by a conventional method and, if necessary, purifying the product by a method such as recrystallization or column chromatography.

In the following, representative compounds of the compounds represented by the general formula (II) which are novel compounds produced by the production method 1- (1) of the present invention are shown in Table 1. However, the present invention is not limited to this. General formula (II)

Embedded image

[0018]

[Table 1]

[0019]

[Table 2]

[0020]

[Table 3]

[0021]

[Table 4]

[0022]

[Table 5]

[0023]

[Table 6] In Table 1, "Ph" indicates a phenyl group, and "c-"
Represents an alicyclic hydrocarbon.

Hereinafter, typical examples of the present invention will be illustrated, but the present invention is not limited thereto.

[Embodiment 1] Production of N- (3-chloro-4-methylphenyl) -4-methyl-1,2,3-thiadiazole-5-carboxamide. 1-1. Production of N- (3-chloro-4-methylphenyl) acetoacetamide.

Embedded image 8.4 g (0.10 mol) of diketene was dissolved in 25 ml of toluene, and added dropwise to a solution of 14.2 g (0.10 mol) of 3-chloro-p-toluidine in 15 ml of toluene at room temperature. After completion of the dropwise addition, the reaction was performed at 80 ° C. for 4 hours.
After completion of the reaction, ethyl acetate was added to the reaction solution, and the organic layer was washed with aqueous hydrochloric acid, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and the obtained residue was recrystallized from 50% ethanol. 0 g of the desired product was obtained. Melting point: 95-
96 ° C, 80% yield. 1-2. N- (3-chloro-4-methylphenyl)-
Production of 3- (2-acetylhydrazono) butanamide.

[0025]

Embedded image 11.3 g (0.05 mol) of N- (3-chloro-4-
(Methylphenyl) acetoacetamide was suspended in 60 ml of water, 4.4 g (0.06 mol) of acetohydrazide and 0.3 g of acetic acid were added with stirring at room temperature, and the reaction was carried out at room temperature for 4 hours. After completion of the reaction, the precipitated crystals were filtered and washed with water to obtain 14.0 g of the desired product. Melting point: 1
83-184 ° C, 99% yield.

1-3. Production of N- (3-chloro-4-methylphenyl) -4-methyl-1,2,3-thiadiazole-5-carboxamide.

Embedded image 11.3 g (0.040 mol) of N- (3-chloro-4
-Methylphenyl) -3- (2-acetylhydrazono)
Butanamide was suspended in 100 ml of monochlorobenzene, and 9.5 g (0.080 mol) of thionyl chloride was added dropwise at room temperature with stirring. After the completion of the dropwise addition, the reaction was carried out at room temperature for 3 hours. After completion of the reaction, the reaction solution was neutralized by adding an aqueous solution of sodium carbonate, and the target product was extracted with ethyl acetate.
The extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure, and the obtained residue was recrystallized from 70% methanol to obtain 7.0 g of the desired product. Melting point: 112-11
3 ° C, 65% yield.

Embodiment 2 FIG. N- (4-methylphenyl)
Production of 4-methyl-1,2,3-thiadiazole-5-carboxamide.

Embedded image 0.40 g (10 mmol) of 63% oily sodium hydride are suspended in 10 ml of tetrahydrofuran and
10 g (10 mmol) of p-toluidine and 1.60 g
(10 mmol) of methyl 4-methyl-1,2,3-thiadiazole-5-carboxylate was added at room temperature, and then 4
The reaction was performed at room temperature for hours. After completion of the reaction, ethyl acetate was added to the reaction system to extract the desired product, and the organic layer was washed with hydrochloric acid, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure.
By washing the obtained residue with n-heptane,
1.90 g of the desired product was obtained. Melting point: 115-117 ° C.
Yield: 81%.

Embodiment 3 FIG. N- (4-methylphenyl)
Production of 4-methyl-1,2,3-thiadiazole-5-carboxamide.

Embedded image 14.0 g (105 mmol) of aluminum chloride in 2
Suspended in 00 ml of dichloroethane, 25m under ice-cooling
33.6 g (314 mmol) of p-toluidine dissolved in 1 dichloroethane were added dropwise over 5 minutes. After dropping, stirring was continued for 30 minutes, and then 20.0 g (purity: 8
2.8%, 105 mmol) of 4-methyl-1,2,3
-Methyl thiadiazole-5-carboxylate to add 50
The reaction was performed at ６０60 ° C. for 6 hours. After completion of the reaction, the reaction solution was poured into 500 ml of ice water, and excess p-toluidine was removed by adding 30 ml of concentrated hydrochloric acid. The organic layer was dried over anhydrous magnesium sulfate, and dichloroethane was distilled off under reduced pressure to obtain 25.4 g of crude crystals of the desired product. The purity of the obtained crude crystals was 92.6% by gas chromatography as compared with the standard. Net yield: 96%

Embodiment 4 FIG. N- (4-methylphenyl)
Production of 4-methyl-1,2,3-thiadiazole-5-carboxamide.

Embedded image 2.06 g (12.7 mmol) of aluminum chloride was suspended in 30 ml of dichloroethane, and 2 ml of the suspension was cooled on ice.
1.35 g (12.7 mmol) of p-toluidine dissolved in dichloroethane were added dropwise. After dropping, 30
Stirring is continued for one minute and then 2.00 g (12.7 mmol)
Of 4-methyl-1,2,3-thiadiazole-5-carboxylate was added thereto, and the reaction was carried out by passing ammonia gas under reflux for 6 hours. After the reaction is completed, add 100 ml of the reaction solution.
And the desired product was extracted with dichloroethane. The organic layer was dried over anhydrous magnesium sulfate, and dichloroethane was distilled off under reduced pressure to obtain 2.43 g of crude crystals of the target product. The obtained crude crystals were found to have a purity of 91% by gas chromatography as compared with the standard. Net yield: 75%

Claims (5)

[Claims] 1. A compound of the general formula (IV)(Where R₁Is a hydrogen atom, C₁-C₆ Alkyl group or C_Three-C₇
R represents a cycloalkyl group;_TwoIs a hydrogen atom, C₁-C₂₀Al
Kill group, halo C₁-C₂₀Alkyl group, C_Two-C₂₀Alkenyl group,
Halo C_Two-C₂₀Alkenyl group, C_Two-C₂₀Alkynyl group, halo C_Two
-C₂₀Alkynyl group, C_Three-C₁₂Cycloalkyl group, C₁-C₆A
Lucoxy C₁-C₆Alkyl group, C₁-C₆Alkoxy C₁-C₆A
Lucoxy C₁-C₆Alkyl group, carboxy C₁-C₆Alkyl
Group, C₁-C ₂₀Alkoxycarbonyl C₁-C₆Alkyl group,
Lubamoyl C₁-C₆Alkyl group, same or different
C₁-C₁₂Alkyl group, phenyl group, or halogen atom
Or C₁-C₆Phenyl group substituted by alkyl group
Substituted carbamo having one or two substituents selected from
Il C₁-C₆Alkyl group, cyano C₁-C₆Alkyl group, C₁-C
₆Alkylcarbonyloxy C₁-C₆Alkyl group, phenyl
Lecarbonyloxy C₁-C₆Alkyl group, same or different
Halogen atom, cyano group, nitro group, C₁-C₆
Alkyl group, halo C₁-C₆Alkyl group, C₁-C₆Alkoxy
Group, halo C₁-C₆Alkoxy group or C₁-C₁₂Alkoxycal
Having 1 to 5 substituents selected from a bonyl group on the ring
Substituted phenylcarbonyloxy C₁-C₆Alkyl group,
Phenyl group, which may be the same or different, a halogen atom,
Ano group, nitro group, C₁-C₆Alkyl group, halo C₁-C₆Al
Kill group, C₁-C₆Alkoxy group, halo C₁-C₆Alkoxy group
Or C₁-C₁₂1 to 1 selected from an alkoxycarbonyl group
Substituted phenyl group having 5 substituents, phenyl C₁-C₆
An alkyl group, which may be the same or different, a halogen atom,
Cyano group, nitro group, C₁-C₆Alkyl group, halo C₁-C₆A
Lucyl group, C₁-C₆Alkoxy group, halo C₁-C₆Alkoxy
Group or C₁-C₁₂1 selected from an alkoxycarbonyl group
Substituted phenyl C having up to 5 substituents on the ring₁-C₆Al
Kill group, C₁-C ₆Alkylcarbonylamino C₁-C₆Archi
Phenylcarbonylamino C₁-C ₆Alkyl group,
May be one or different, halogen atom, cyano group, nitro
B group, C₁-C₆Alkyl group, halo C₁-C₆Alkyl group, C₁-C
₆Alkoxy group, halo C₁-C₆Alkoxy group or C₁-C₁₂A
1 to 5 substituents selected from alkoxycarbonyl groups
Phenylcarbonylamino C having on the ring₁-C₆A
Alkyl group, which may be the same or different, oxygen atom, sulfur atom
Has one or more heteroatoms selected from
5 to 6-membered heterocyclic ring, which may be the same or different,
Atom, cyano group, nitro group, C₁-C₆Alkyl group, halo
C₁-C₆Alkyl group, C₁-C₆Alkoxy group, halo C₁-C₆A
Lucoxy group or C₁-C₁₂Select from alkoxycarbonyl groups
Having 1 to 5 substituents on a ring, an oxygen atom, a sulfur
May be the same or different selected from atoms or nitrogen atoms
A substituted 5- to 6-membered heterocycle having at least one heteroatom,
Oxygen atom, sulfur atom or nitrogen atom
5 or 6 members having one or more heteroatoms selected from offspring
Heterocycle C₁-C₆Alkyl groups, which may be the same or different,
Logen atom, cyano group, nitro group, C₁-C₆Alkyl group,
Halo C₁-C₆Alkyl group, C₁-C₆Alkoxy group, halo C₁-C
₆Alkoxy group or C₁-C₁₂From an alkoxycarbonyl group
Having 1 to 5 substituents selected on the ring, an oxygen atom,
Same or different selected from sulfur atom or nitrogen atom
Substituted 5- to 6-membered heterocycles having one or more heteroatoms
C₁-C₆An alkyl group, which may be the same or different,
One or more hetero atoms selected from the group consisting of
5- to 6-membered heterocyclic ring C having a hydrogen atom₁-C ₆Carbonyloxy
An alkyl group, which may be the same or different, a halogen atom,
Cyano group, nitro group, C₁-C₆Alkyl group, halo C₁-C₆A
Lucyl group, C₁-C₆Alkoxy group, halo C₁-C₆Alkoxy
Group or C₁-C₁₂1 selected from an alkoxycarbonyl group
Having up to 5 substituents on the ring, an oxygen atom, a sulfur atom or
One or more which may be the same or different selected from nitrogen atoms
5 to 6-membered heterocyclic carbonyl group having a hetero atom
Kiss C₁-C₆Alkyl group, which may be the same or different, oxygen
One or more atoms selected from atoms, sulfur atoms or nitrogen atoms
5- to 6-membered heterocyclic carbonylamino C having a terror atom₁-C
₆An alkyl group or the same or different
Atom, cyano group, nitro group, C₁-C₆Alkyl group, halo
C₁-C₆Alkyl group, C₁-C₆Alkoxy group, halo C₁-C₆A
Lucoxy group or C₁-C₁₂Select from alkoxycarbonyl groups
Having 1 to 5 substituents on a ring, an oxygen atom, a sulfur
May be the same or different selected from atoms or nitrogen atoms
Substituted 5- to 6-membered heterocyclic kar having one or more heteroatoms
Bonylamino C₁-C₆Represents an alkyl group, and Y is -O-,-
S- or -N (R_Four)-(Where R_FourIs a hydrogen atom or C₁-
C₆Shows an alkyl group. ). Compound represented by)
And the general formula (III)_ThreeNHNH_Two (III) (wherein, R_ThreeIs C₁-C₂₀Alkylcarbonyl group, halo C₁-C
₂₀Alkylcarbonyl group, C_Three-C₁₂Cycloalkylcarbo
Nyl group, hydroxy C₁-C₂₀Alkylcarbonyl group, shea
No C₁-C₂₀Alkylcarbonyl group, C₁-C₂₀Alkoxycal
Bonyl group, C₁-C ₂₀Alkoxy C₁-C₂₀Alkylcarbonyl
Group, a phenylcarbonyl group, which may be the same or different,
Halogen atom, cyano group, nitro group, C₁-C₆Alkyl
Group, halo C₁-C₆Alkyl group, C₁-C₆Alkoxy group, halo
C₁-C₆Alkoxy group or C₁-C₁₂Alkoxycarbonyl group
Substituted 1 to 5 substituents on the ring selected from
Phenylcarbonyl group, phenyl C₁-C₆Alkyl carboni
Groups, which may be the same or different, a halogen atom, a cyano
Group, nitro group, C₁-C₆Alkyl group, halo C₁-C₆Alkyl
Group, C₁-C₆Alkoxy group, halo C₁-C₆An alkoxy group or
C₁-C₁₂1 to 5 selected from alkoxycarbonyl groups
Phenyl C having a substituent on the ring₁-C₆Alkylka
Rubonyl group, carbamoyl group, C₁-C₂₀Alkylsulfoni
Le group, halo C₁-C ₂₀Alkylsulfonyl group, C_Three-C₁₂Cyclo
Alkylsulfonyl group, phenylsulfonyl group or the same
Or a halogen atom, a cyano group,
Toro group, C₁-C₆Alkyl group, halo C₁-C₆Alkyl group, C₁
-C₆Alkoxy group, halo C₁-C₆Alkoxy group or C₁-C₁₂
1 to 5 substitutions selected from alkoxycarbonyl groups
A substituted phenylsulfonyl group having a group on the ring is shown. )
By reacting with a hydrazine represented by the general formula (II):(Where R₁, R_Two, R_ThreeAnd Y are the same as above. )
The compound (II) is isolated or not isolated
To react with thionyl chloride or sulfur dichloride
General formula (I)(Where R₁, R_TwoAnd Y are the same as above. )
A method for producing a 1,2,3-thiadiazole derivative. 2. A compound of the general formula (IV)(Where R₁Is a hydrogen atom, C₁-C₆ Alkyl group or C_Three-C₇
R represents a cycloalkyl group;_TwoIs a hydrogen atom, C₁-C₂₀Al
Kill group, halo C₁-C₂₀Alkyl group, C_Two-C₂₀Alkenyl group,
Halo C_Two-C₂₀Alkenyl group, C_Two-C₂₀Alkynyl group, halo C_Two
-C₂₀Alkynyl group, C_Three-C₁₂Cycloalkyl group, C₁-C₆A
Lucoxy C₁-C₆Alkyl group, C₁-C₆Alkoxy C₁-C₆A
Lucoxy C₁-C₆Alkyl group, carboxy C₁-C₆Alkyl
Group, C₁-C ₂₀Alkoxycarbonyl C₁-C₆Alkyl group,
Lubamoyl C₁-C₆Alkyl group, same or different
C₁-C₁₂Alkyl group, phenyl group or halogen atom
Or C₁-C₆Is it a phenyl group substituted by an alkyl group?
Substituted carbamoy having one or two substituents selected from
Le C₁-C₆Alkyl group, cyano C₁-C₆Alkyl group, C₁-C ₆
Alkylcarbonyloxy C₁-C₆Alkyl group, phenyl
Carbonyloxy C₁-C ₆Alkyl groups, identical or different
Good, halogen atom, cyano group, nitro group, C₁-C₆A
Lucyl group, halo C₁-C₆Alkyl group, C₁-C₆Alkoxy
Group, halo C₁-C₆Alkoxy group or C₁-C₁₂Alkoxycal
Having 1 to 5 substituents selected from a bonyl group on the ring
Substituted phenylcarbonyloxy C₁-C₆Alkyl group,
Phenyl group, which may be the same or different, a halogen atom,
Ano group, nitro group, C₁-C₆Alkyl group, halo C₁-C₆Al
Kill group, C₁-C₆Alkoxy group, halo C₁-C₆Alkoxy group
Or C₁-C₁₂1 to 1 selected from an alkoxycarbonyl group
Substituted phenyl group having 5 substituents, phenyl C₁-C₆
An alkyl group, which may be the same or different, a halogen atom,
Cyano group, nitro group, C₁-C₆Alkyl group, halo C₁-C₆A
Lucyl group, C₁-C₆Alkoxy group, halo C₁-C₆Alkoxy
Group or C₁-C₁₂1 selected from an alkoxycarbonyl group
Substituted phenyl C having up to 5 substituents on the ring₁-C₆Al
Kill group, C₁-C₆Alkylcarbonylamino C₁-C₆Archi
Phenylcarbonylamino C₁-C₆Alkyl group,
May be one or different, halogen atom, cyano group, nitro
B group, C₁-C₆Alkyl group, halo C₁-C₆Alkyl group, C₁-C
₆Alkoxy group, halo C₁-C₆Alkoxy group or C₁-C₁₂A
1 to 5 substituents selected from alkoxycarbonyl groups
Phenylcarbonylamino C having on the ring₁-C₆A
Alkyl group, which may be the same or different, oxygen atom, sulfur atom
Has one or more heteroatoms selected from
5 to 6-membered heterocyclic ring, which may be the same or different,
Atom, cyano group, nitro group, C₁-C₆Alkyl group, halo
C₁-C₆Alkyl group, C₁-C₆Alkoxy group, halo C₁-C₆A
Lucoxy group or C₁-C₁₂Select from alkoxycarbonyl groups
Having 1 to 5 substituents on a ring, an oxygen atom, a sulfur
May be the same or different selected from atoms or nitrogen atoms
A substituted 5- to 6-membered heterocycle having at least one heteroatom,
Oxygen atom, sulfur atom or nitrogen atom
5 or 6 members having one or more heteroatoms selected from offspring
Heterocycle C₁-C₆Alkyl groups, which may be the same or different,
Logen atom, cyano group, nitro group, C₁-C₆Alkyl group,
Halo C₁-C₆Alkyl group, C₁-C₆Alkoxy group, halo C₁-C
₆Alkoxy group or C₁-C₁₂From an alkoxycarbonyl group
Having 1 to 5 substituents selected on the ring, an oxygen atom,
Same or different selected from sulfur atom or nitrogen atom
Substituted 5- to 6-membered heterocycles having one or more heteroatoms
C₁-C₆An alkyl group, which may be the same or different,
One or more hetero atoms selected from the group consisting of
5- to 6-membered heterocyclic carbonyloxy C-atoms₁-C₆
An alkyl group, which may be the same or different, a halogen atom,
Cyano group, nitro group, C₁-C₆Alkyl group, halo C₁-C₆A
Lucyl group, C₁-C₆Alkoxy group, halo C₁-C₆Alkoxy
Group or C₁-C₁₂1 selected from an alkoxycarbonyl group
Having up to 5 substituents on the ring, an oxygen atom, a sulfur atom or
One or more which may be the same or different selected from nitrogen atoms
5 to 6-membered heterocyclic carbonyl group having a hetero atom
Kiss C₁-C₆Alkyl group, which may be the same or different, oxygen
One or more atoms selected from atoms, sulfur atoms or nitrogen atoms
5- to 6-membered heterocyclic carbonylamino C having a terror atom₁-C
₆An alkyl group or the same or different
Atom, cyano group, nitro group, C₁-C₆Alkyl group, halo
C₁-C₆Alkyl group, C₁-C₆Alkoxy group, halo C₁-C₆A
Lucoxy group or C₁-C₁₂Select from alkoxycarbonyl groups
Having 1 to 5 substituents on a ring, an oxygen atom, a sulfur
May be the same or different selected from atoms or nitrogen atoms
Substituted 5- to 6-membered heterocyclic kar having one or more heteroatoms
Bonylamino C₁-C₆Represents an alkyl group, and Y is -O-,-
S- or -N (R_Four)-(Where R_FourIs a hydrogen atom or C₁
-C₆Shows an alkyl group. ). Compound represented by)
And the general formula (III)_ThreeNHNH_Two (III) (wherein, R_ThreeIs C₁-C₂₀Alkylcarbonyl group, halo C₁-C
₂₀Alkylcarbonyl group, C_Three-C₁₂Cycloalkylcarbo
Nyl group, hydroxy C₁-C₂₀Alkylcarbonyl group, shea
No C₁-C₂₀Alkylcarbonyl group, C₁-C₂₀Alkoxycal
Bonyl group, C₁-C ₂₀Alkoxy C₁-C₂₀Alkylcarbonyl
Group, a phenylcarbonyl group, which may be the same or different,
Halogen atom, cyano group, nitro group, C₁-C₆Alkyl
Group, halo C₁-C₆Alkyl group, C₁-C₆Alkoxy group, halo
C₁-C₆Alkoxy group or C₁-C₁₂Alkoxycarbonyl group
Substituted 1 to 5 substituents on the ring selected from
Phenylcarbonyl group, phenyl C₁-C₆Alkyl carboni
Groups, which may be the same or different, a halogen atom, a cyano
Group, nitro group, C₁-C₆Alkyl group, halo C₁-C₆Alkyl
Group, C₁-C₆Alkoxy group, halo C₁-C₆An alkoxy group or
C₁-C₁₂1 to 5 selected from alkoxycarbonyl groups
Phenyl C having a substituent on the ring₁-C₆Alkylka
Rubonyl group, carbamoyl group, C₁-C₂₀Alkylsulfoni
Le group, halo C₁-C ₂₀Alkylsulfonyl group, C_Three-C₁₂Cyclo
Alkylsulfonyl group, phenylsulfonyl group or the same
Or a halogen atom, a cyano group,
Toro group, C₁-C₆Alkyl group, halo C₁-C₆Alkyl group, C₁
-C₆Alkoxy group, halo C₁-C₆Alkoxy group or C₁-C₁₂
1 to 5 substitutions selected from alkoxycarbonyl groups
A substituted phenylsulfonyl group having a group on the ring is shown. )
Characterized by reacting with hydrazines represented by
General formula (II)(Where R₁, R_Two, R_ThreeAnd Y are the same as above. )
For producing a compound to be produced. 3. A compound of the general formula (II)(Where R₁Is a hydrogen atom, C₁-C₆ Alkyl group or C_Three-C₇
R represents a cycloalkyl group;_TwoIs a hydrogen atom, C₁-C₂₀Al
Kill group, halo C₁-C₂₀Alkyl group, C_Two-C₂₀Alkenyl group,
Halo C_Two-C₂₀Alkenyl group, C_Two-C₂₀Alkynyl group, halo C_Two
-C₂₀Alkynyl group, C_Three-C₁₂Cycloalkyl group, C₁-C₆A
Lucoxy C₁-C₆Alkyl group, C₁-C₆Alkoxy C₁-C₆A
Lucoxy C₁-C₆Alkyl group, carboxy C₁-C₆Alkyl
Group, C₁-C ₂₀Alkoxycarbonyl C₁-C₆Alkyl group,
Lubamoyl C₁-C₆Alkyl group, same or different
C₁-C₁₂Alkyl group, phenyl group, halogen atom or
C₁-C ₆Select from phenyl groups substituted by alkyl groups
Substituted carbamoyl C having 1 to 2 substituents₁-C
₆Alkyl group, cyano C₁-C₆Alkyl group, C₁-C₆Archi
Lecarbonyloxy C₁-C₆Alkyl group, phenylcarbo
Nyloxy C₁-C₆Alkyl group, same or different
, Halogen atom, cyano group, nitro group, C₁-C₆Archi
Le group, halo C₁-C₆Alkyl group, C₁-C₆Alkoxy group, ha
B c₁-C₆Alkoxy group or C₁-C₁₂Alkoxycarbonyl
Having 1 to 5 substituents selected from the group
Nylcarbonyloxy C₁-C₆Alkyl group, phenyl group,
May be the same or different, and may be a halogen atom, a cyano group,
Toro group, C₁-C₆Alkyl group, halo C₁-C₆Alkyl group, C₁
-C₆Alkoxy group, halo C₁-C₆Alkoxy group or C₁-C₁₂
1 to 5 substitutions selected from alkoxycarbonyl groups
Substituted phenyl group having a group, phenyl C₁-C₆Alkyl
Groups, which may be the same or different, a halogen atom, a cyano
Group, nitro group, C₁-C₆Alkyl group, halo C₁-C₆Alkyl
Group, C₁-C₆Alkoxy group, halo C₁-C₆An alkoxy group or
C₁-C₁₂1 to 5 selected from alkoxycarbonyl groups
Phenyl C having a substituent on the ring₁-C₆Alkyl
Group, C₁-C₆Alkylcarbonylamino C₁-C₆Alkyl
Group, phenylcarbonylamino C₁-C₆Alkyl group, identical
Or may be different, a halogen atom, a cyano group, a nitro
Group, C₁-C₆Alkyl group, halo C₁-C₆Alkyl group, C₁-C₆
Alkoxy group, halo C₁-C₆Alkoxy group or C₁-C₁₂Al
1 to 5 substituents selected from a carbonyl group
Substituted phenylcarbonylamino C on the ring₁-C₆Al
A kill group, which may be the same or different, an oxygen atom, a sulfur atom
Or has one or more hetero atoms selected from nitrogen atoms
5 to 6-membered heterocyclic ring, which may be the same or different, and halogen
Atom, cyano group, nitro group, C₁-C₆Alkyl group, halo C₁
-C₆Alkyl group, C₁-C₆Alkoxy group, halo C₁-C₆Al
Coxy group or C₁-C₁₂Selected from alkoxycarbonyl groups
Having 1 to 5 substituents on the ring, an oxygen atom, a sulfur atom
May be the same or different selected from
Substituted 5- to 6-membered heterocycle having one or more heteroatoms, identical
Or may be different, an oxygen atom, a sulfur atom or a nitrogen atom
5 or 6 membered compound having one or more heteroatoms selected from
Ring C₁-C₆Alkyl group, which may be the same or different, halo
Gen atom, cyano group, nitro group, C₁-C₆Alkyl group, ha
B c₁-C₆Alkyl group, C₁-C₆Alkoxy group, halo C₁-C₆
Alkoxy group or C₁-C₁₂Select from alkoxycarbonyl groups
Having 1 to 5 substituents selected on a ring, an oxygen atom,
Same or different, selected from a yellow atom or a nitrogen atom
Substituted 5-6 membered heterocycle C having good one or more heteroatoms₁
-C₆An alkyl group, which may be the same or different, an oxygen atom,
One or more hetero atoms selected from sulfur or nitrogen atoms
5- or 6-membered heterocyclic carbonyloxy C₁-C₆Al
A kill group, which may be the same or different, a halogen atom,
No group, nitro group, C₁-C₆Alkyl group, halo C₁-C₆Archi
Group, C₁-C₆Alkoxy group, halo C₁-C ₆Alkoxy group or
Is C₁-C₁₂1 to 5 selected from an alkoxycarbonyl group
Oxygen atom, sulfur atom or nitrogen
One or more of the same or different atoms selected from atoms
Substituted 5- or 6-membered heterocyclic carbonyloxy having a telo atom
C₁-C₆An alkyl group, which may be the same or different,
One or more hetero atoms selected from the group consisting of
5- to 6-membered heterocyclic carbonylamino C having a hydrogen atom₁-C₆
An alkyl group or a halogen, which may be the same or different,
Atom, cyano group, nitro group, C₁-C₆Alkyl group, halo C₁
-C₆Alkyl group, C₁-C₆Alkoxy group, halo C₁-C₆Al
Coxy group or C₁-C₁₂Selected from alkoxycarbonyl groups
Having 1 to 5 substituents on the ring, an oxygen atom, a sulfur atom
May be the same or different selected from
5- or 6-membered heterocyclic carbonyl having one or more heteroatoms
Amino C₁-C₆Y represents -O-, -S- or an alkyl group;
Is -N (R_Four)-(Where R_FourIs a hydrogen atom or C₁-C₆A
Represents a alkyl group), and R_ThreeIs C₁-C₂₀Alkyl carb
Nyl group, halo C₁-C₂₀Alkylcarbonyl group, C_Three-C₁₂Shiku
Loalkylcarbonyl group, hydroxy C₁-C₂₀Alkylka
Rubonyl group, cyano C₁-C₂₀Alkylcarbonyl group, C₁-C
₂₀Alkoxycarbonyl group, C₁-C₂₀Alkoxy C₁-C₂₀A
Alkylcarbonyl group, phenylcarbonyl group, same or
May be different, a halogen atom, a cyano group, a nitro group,
C₁-C₆Alkyl group, halo C₁-C₆Alkyl group, C₁-C₆Al
Coxy group, halo C₁-C₆Alkoxy group or C₁-C₁₂Alkoki
1 to 5 substituents selected from a cyclic group
Substituted phenylcarbonyl group, phenyl C₁-C₆A
Alkylcarbonyl group, which may be the same or different,
Atom, cyano group, nitro group, C₁-C₆Alkyl group, halo
C₁-C₆Alkyl group, C₁-C₆Alkoxy group, halo C₁-C₆A
Lucoxy group or C₁-C₁₂Select from alkoxycarbonyl groups
Substituted phenyl C having 1 to 5 substituents on the ring₁
-C₆Alkylcarbonyl group, carbamoyl group, C₁-C₂₀A
Rukylsulfonyl group, halo C₁-C₂₀Alkylsulfonyl
Group, C_Three-C₁₂Cycloalkyl sulfonyl group, phenyl sulf
A phonyl group or a halogen atom
Child, cyano group, nitro group, C₁-C₆Alkyl group, halo C₁-C
₆Alkyl group, C₁-C₆Alkoxy group, halo C₁-C₆Arco
Xyl group or C₁-C₁₂Selected from alkoxycarbonyl groups
Substituted phenylsulfo having 1 to 5 substituents on the ring
Represents a nyl group. Where R₁Is a methyl group and Y is -NH-
And R_ThreeRepresents a phenylcarbonyl group;_Two
Is a phenyl group, R₁Is a methyl group and R_TwoIs replaced
Y represents -NH-; R represents_ThreeIs phenyl
When it represents a carbonyl group, R_TwoAnd a substituent of the phenyl group of
To give 2-chloro, 3-chloro, 4-chloro, 2,
5-dichloro, 2-bromo, 2-methyl, 4-methyl
Butyl, 2,4-dimethyl, 2-methoxy, 4-methyl
A toxic group, a 2,4-dimethoxy group, a 4-ethoxy group,
R, except for the 2,4-dimethoxy group,₁Is a methyl group and Y is
-NH-, R_ThreeRepresents a carbamoyl group,
_TwoIs a phenyl group, R₁Is a methyl group and R_TwoIs replaced
A phenyl group; Y represents -NH-;_ThreeIs carb
When it represents a moyl group, R_TwoAs a substituent of the phenyl group of
2-chloro, 3-chloro, 4-chloro, 4-bromo
Mo group, 4-iodo group, 2,5-dichloro group, 2-chloro
-4-iodo group, 2,4-dimethyl group, 2,4-dimethoate
Excludes xy and 4-ethoxy groups. ). 4. A compound of the general formula (II)(Where R₁Is a hydrogen atom, C₁-C₆ Alkyl group or C_Three-C₇
R represents a cycloalkyl group;_TwoIs a hydrogen atom, C₁-C₂₀Al
Kill group, halo C₁-C₂₀Alkyl group, C_Two-C₂₀Alkenyl group,
Halo C_Two-C₂₀Alkenyl group, C_Two-C₂₀Alkynyl group, halo C_Two
-C₂₀Alkynyl group, C_Three-C₁₂Cycloalkyl group, C₁-C₆A
Lucoxy C₁-C₆Alkyl group, C₁-C₆Alkoxy C₁-C₆A
Lucoxy C₁-C₆Alkyl group, carboxy C₁-C₆Alkyl
Group, C₁-C ₂₀Alkoxycarbonyl C₁-C₆Alkyl group,
Lubamoyl C₁-C₆Alkyl group, same or different
C₁-C₁₂Alkyl group, phenyl group, halogen atom or
C₁-C ₆Select from phenyl groups substituted by alkyl groups
Substituted carbamoyl C having 1 to 2 substituents₁-C
₆Alkyl group, cyano C₁-C₆Alkyl group, C₁-C₆Archi
Lecarbonyloxy C₁-C₆Alkyl group, phenylcarbo
Nyloxy C₁-C₆Alkyl group, same or different
, Halogen atom, cyano group, nitro group, C₁-C₆Archi
Le group, halo C₁-C₆Alkyl group, C₁-C₆Alkoxy group, ha
B c₁-C₆Alkoxy group or C₁-C₁₂Alkoxycarbonyl
Having 1 to 5 substituents selected from the group
Nylcarbonyloxy C₁-C₆Alkyl group, phenyl group,
May be the same or different, and may be a halogen atom, a cyano group,
Toro group, C₁-C₆Alkyl group, halo C₁-C₆Alkyl group, C₁
-C₆Alkoxy group, halo C₁-C₆Alkoxy group or C₁-C₁₂
1 to 5 substitutions selected from alkoxycarbonyl groups
Substituted phenyl group having a group, phenyl C₁-C₆Alkyl
Groups, which may be the same or different, a halogen atom, a cyano
Group, nitro group, C₁-C₆Alkyl group, halo C₁-C₆Alkyl
Group, C₁-C₆Alkoxy group, halo C₁-C₆An alkoxy group or
C₁-C₁₂1 to 5 selected from alkoxycarbonyl groups
Phenyl C having a substituent on the ring₁-C₆Alkyl
Group, C₁-C₆Alkylcarbonylamino C₁-C₆Alkyl
Group, phenylcarbonylamino C₁-C₆Alkyl group, identical
Or may be different, a halogen atom, a cyano group, a nitro
Group, C₁-C₆Alkyl group, halo C₁-C₆Alkyl group, C₁-C₆
Alkoxy group, halo C₁-C₆Alkoxy group or C₁-C₁₂Al
1 to 5 substituents selected from a carbonyl group
Substituted phenylcarbonylamino C on the ring₁-C₆Al
A kill group, which may be the same or different, an oxygen atom, a sulfur atom
Or has one or more hetero atoms selected from nitrogen atoms
5 to 6-membered heterocyclic ring, which may be the same or different, and halogen
Atom, cyano group, nitro group, C₁-C₆Alkyl group, halo C₁
-C₆Alkyl group, C₁-C₆Alkoxy group, halo C₁-C₆Al
Coxy group or C₁-C₁₂Selected from alkoxycarbonyl groups
Having 1 to 5 substituents on the ring, an oxygen atom, a sulfur atom
May be the same or different selected from
Substituted 5- to 6-membered heterocycle having one or more heteroatoms, identical
Or may be different, an oxygen atom, a sulfur atom or a nitrogen atom
5 or 6 membered compound having one or more heteroatoms selected from
Ring C₁-C₆Alkyl group, which may be the same or different, halo
Gen atom, cyano group, nitro group, C₁-C₆Alkyl group, ha
B c₁-C₆Alkyl group, C₁-C₆Alkoxy group, halo C₁-C₆
Alkoxy group or C₁-C₁₂Select from alkoxycarbonyl groups
Having 1 to 5 substituents selected on a ring, an oxygen atom,
Same or different, selected from a yellow atom or a nitrogen atom
Substituted 5-6 membered heterocycle C having good one or more heteroatoms₁
-C₆An alkyl group, which may be the same or different, an oxygen atom,
One or more hetero atoms selected from sulfur or nitrogen atoms
5- or 6-membered heterocyclic carbonyloxy C₁-C₆Al
A kill group, which may be the same or different, a halogen atom,
No group, nitro group, C₁-C₆Alkyl group, halo C₁-C₆Archi
Group, C₁-C₆Alkoxy group, halo C₁-C ₆Alkoxy group or
Is C₁-C₁₂1 to 5 selected from an alkoxycarbonyl group
Oxygen atom, sulfur atom or nitrogen
One or more of the same or different atoms selected from atoms
Substituted 5- or 6-membered heterocyclic carbonyloxy having a telo atom
C₁-C₆An alkyl group, which may be the same or different,
One or more hetero atoms selected from the group consisting of
5- to 6-membered heterocyclic carbonylamino C having a hydrogen atom₁-C₆
An alkyl group or a halogen, which may be the same or different,
Atom, cyano group, nitro group, C₁-C₆Alkyl group, halo C₁
-C₆Alkyl group, C₁-C₆Alkoxy group, halo C₁-C₆Al
Coxy group or C₁-C₁₂Selected from alkoxycarbonyl groups
Having 1 to 5 substituents on the ring, an oxygen atom, a sulfur atom
May be the same or different selected from
5- or 6-membered heterocyclic carbonyl having one or more heteroatoms
Amino C₁-C₆Y represents -O-, -S- or an alkyl group;
Is -N (R_Four)-(Where R_FourIs a hydrogen atom or C₁-C₆A
Represents a alkyl group), and R_ThreeIs C₁-C₂₀Alkyl carb
Nyl group, halo C₁-C₂₀Alkylcarbonyl group, C_Three-C₁₂Shiku
Loalkylcarbonyl group, hydroxy C₁-C₂₀Alkylka
Rubonyl group, cyano C₁-C₂₀Alkylcarbonyl group, C₁-C
₂₀Alkoxycarbonyl group, C₁-C₂₀Alkoxy C₁-C₂₀A
Alkylcarbonyl group, phenylcarbonyl group, same or
May be different, a halogen atom, a cyano group, a nitro group,
C₁-C₆Alkyl group, halo C₁-C₆Alkyl group, C₁-C₆Al
Coxy group, halo C₁-C₆Alkoxy group or C₁-C₁₂Alkoki
1 to 5 substituents selected from a cyclic group
Substituted phenylcarbonyl group, phenyl C₁-C₆A
Alkylcarbonyl group, which may be the same or different,
Atom, cyano group, nitro group, C₁-C₆Alkyl group, halo
C₁-C₆Alkyl group, C₁-C₆Alkoxy group, halo C₁-C₆A
Lucoxy group or C₁-C₁₂Select from alkoxycarbonyl groups
Substituted phenyl C having 1 to 5 substituents on the ring₁
-C₆Alkylcarbonyl group, carbamoyl group, C₁-C₂₀A
Rukylsulfonyl group, halo C₁-C₂₀Alkylsulfonyl
Group, C_Three-C₁₂Cycloalkyl sulfonyl group, phenyl sulf
A phonyl group or a halogen atom
Child, cyano group, nitro group, C₁-C₆Alkyl group, halo C₁-C
₆Alkyl group, C₁-C₆Alkoxy group, halo C₁-C₆Arco
Xyl group or C₁-C₁₂Selected from alkoxycarbonyl groups
Substituted phenylsulfo having 1 to 5 substituents on the ring
Represents a nyl group. ) And the compound (II)
Or thionyl chloride or sulfur dichloride without isolation
General formula (I) characterized by reacting with yellow(Where R₁, R_TwoAnd Y are the same as above. )
A method for producing a 1,2,3-thiadiazole derivative. 5. A compound of the general formula (I ′)(Where R₁Is a hydrogen atom, C₁-C₆ Alkyl group or C_Three-C₇
R represents a cycloalkyl group;_Two'Is C₁-C_ThreeRepresents an alkyl group
You. 1,2,3-thiadiazole derivative represented by
General formula (III ′)_Four-NH-R_Two (III ′) (wherein, R_TwoIs a hydrogen atom, C₁-C₂₀Alkyl group, halo C₁-C
₂₀Alkyl group, C_Two-C₂₀Alkenyl group, halo C_Two-C₂₀Arche
Nyl group, C_Two-C₂₀Alkynyl group, halo C_Two-C₂₀Alkynyl
Group, C_Three-C₁₂Cycloalkyl group, C₁-C₆Alkoxy C₁-C₆
Alkyl group, C₁-C ₆Alkoxy C₁-C₆Alkoxy C₁-C₆
Alkyl group, carboxy C₁-C₆Alkyl group, C₁-C₂₀Al
Coxycarbonyl C₁-C₆Alkyl group, carbamoyl C₁-C
₆An alkyl group, which may be the same or different, C₁-C₁₂Archi
Group, phenyl group, halogen atom or C₁-C₆Alkyl group
1 to 2 phenyl groups substituted by
Substituted carbamoyl C having a substituent₁-C₆Alkyl group,
Ano C₁-C₆Alkyl group, C₁-C ₆Alkylcarbonyloxy
C₁-C₆Alkyl group, phenylcarbonyloxy C₁-C ₆
An alkyl group, which may be the same or different, a halogen atom,
Cyano group, nitro group, C₁-C₆Alkyl group, halo C₁-C₆A
Lucyl group, C₁-C₆Alkoxy group, halo C₁-C₆Alkoxy
Group or C₁-C₁₂1 selected from an alkoxycarbonyl group
Phenylcarbonyloxy having up to 5 substituents on the ring
C₁-C₆Alkyl group, phenyl group, same or different
Good, halogen atom, cyano group, nitro group, C₁-C₆Al
Kill group, halo C₁-C₆Alkyl group, C₁-C₆An alkoxy group,
Halo C₁-C₆Alkoxy group or C₁-C ₁₂Alkoxycarboni
Substituted with 1 to 5 substituents selected from
Nyl group, phenyl C₁-C₆Alkyl groups, identical or different
Good, halogen atom, cyano group, nitro group, C₁-C₆A
Lucyl group, halo C₁-C₆Alkyl group, C₁-C₆Alkoxy
Group, halo C₁-C₆Alkoxy group or C₁-C₁₂Alkoxycal
Having 1 to 5 substituents selected from a bonyl group on the ring
Substituted phenyl C₁-C₆Alkyl group, C₁-C₆Alkyl cal
Bonylamino C₁-C₆Alkyl group, phenylcarbonyl
Mino C₁-C₆Alkyl group, which may be the same or different, halo
Gen atom, cyano group, nitro group, C₁-C₆Alkyl group, ha
B c₁-C₆Alkyl group, C₁-C₆Alkoxy group, halo C₁-C₆
Alkoxy group or C₁-C₁₂Select from alkoxycarbonyl groups
Substituted phenyl having 1 to 5 substituents selected on the ring
Carbonylamino C₁-C₆Alkyl groups, identical or different
Also selected from oxygen, sulfur or nitrogen atoms
A 5- or 6-membered heterocycle having one or more heteroatoms,
May be different, a halogen atom, a cyano group, a nitro
Group, C₁-C₆Alkyl group, halo C₁-C₆Alkyl group, C₁-C₆
Alkoxy group, halo C₁-C₆Alkoxy group or C₁-C₁₂Al
1 to 5 substituents selected from a carbonyl group
Select from oxygen, sulfur or nitrogen atoms on the ring
With one or more heteroatoms which may be the same or different
5 to 6-membered heterocyclic ring, which may be the same or different,
One or more hetero atoms selected from the group consisting of
5- to 6-membered heterocyclic ring C having a hydrogen atom₁-C₆Alkyl group, identical
Or may be different, a halogen atom, a cyano group, a nitro
Group, C₁-C₆Alkyl group, halo C₁-C₆Alkyl group, C₁-C₆
Alkoxy group, halo C₁-C₆Alkoxy group or C₁-C₁₂Al
1 to 5 substituents selected from a carbonyl group
Select from oxygen, sulfur or nitrogen atoms on the ring
With one or more heteroatoms which may be the same or different
5-6 membered heterocyclic carbonyloxy C₁-C₆Alkyl
Groups, which may be the same or different, an oxygen atom, a sulfur atom or
5 having one or more hetero atoms selected from nitrogen atoms
~ 6 membered heterocyclic C₁-C₆Alkyl group, same or different
, Halogen atom, cyano group, nitro group, C₁-C₆Archi
Le group, halo C₁-C₆Alkyl group, C₁-C₆Alkoxy group, ha
B c₁-C₆Alkoxy group or C₁-C₁₂Alkoxycarbonyl
Having 1 to 5 substituents on the ring selected from the group
Same or different selected from atoms, sulfur atoms or nitrogen atoms
5- or 6-membered complex having one or more heteroatoms which may be
Ring carbonyloxy C₁-C₆Alkyl group, same or different
May be selected from oxygen, sulfur and nitrogen atoms.
5- or 6-membered heterocyclic carboxy having one or more heteroatoms
Nilamino C₁-C₆Alkyl group or same or different
Good, halogen atom, cyano group, nitro group, C₁-C₆A
Lucyl group, halo C₁-C₆Alkyl group, C₁-C₆Alkoxy
Group, halo C₁-C₆Alkoxy group or C₁-C₁₂Alkoxycal
Having 1 to 5 substituents selected from a bonyl group on the ring
Selected from oxygen, sulfur or nitrogen
Or 5-6 with one or more heteroatoms which may be different
Membered heterocyclic carbonylamino C₁-C₆Alkyl group or the same
Or halogen atoms, cyano groups, nitro
Group, C₁-C₆Alkyl group, halo C₁-C₆Alkyl group, C₁-C₆
Alkoxy group, halo C₁-C₆Alkoxy group or C₁-C₁₂Al
1 to 5 substituents selected from a carbonyl group
Select from oxygen, sulfur or nitrogen atoms on the ring
With one or more heteroatoms which may be the same or different
5- to 6-membered heterocyclic carbonylamino C₁-C₆Alkyl group
And R_FourIs a hydrogen atom or C₁-C₆Represents an alkyl group
You. ) Reacting the amines represented by
General formula (I '')(Where R₁, R_TwoAnd R_FourIs the same as above. )
For producing 1,2,3-thiadiazole derivatives.